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Stewart

$263+ Cheap flights from Trinidad to New Windsor (SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
POS — SWF
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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Cheap flight deals from Trinidad to Stewart

Keep the following information in mind while searching for Trinidad to Stewart flight deals. Data was last updated August 17, 2025.

Round-trip from

$459
(Kiwi.com)

One-way from

$263
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$492
From Trinidad to New Windsor Stewart
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One-way flight from Trinidad to New Windsor Stewart
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Highest demand for flights based on searches. 9% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Trinidad to Stewart

Cheapest flights from Trinidad to Stewart
Explore the most affordable flight options available from Trinidad to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:10 amPOS - SWF
1 stop24h 41mMultiple Airlines
Mon 10/1311:01 amSWF - POS
1 stop8h 59mMultiple Airlines
Deal found 8/16$459

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 17, 2025.
Use the filters below to find and compare flights from Trinidad to New Windsor that are best for you.

Fly from

Trinidad

Fly to

Stewart

Route

Depart

Return

Price

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Thu 10/9

10:10 am-10:51 am

1 stop24h 41m

New Windsor Stewart

Mon 10/13

11:01 am-8:00 pm

1 stop8h 59m

$459

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sun 10/26

10:10 am-2:11 pm

1 stop28h 01m

$263

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 8/29

10:10 am-11:23 am

2 stops49h 13m

$364

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sun 8/31

10:10 am-1:05 pm

1 stop26h 55m

$394

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Thu 8/28

10:10 am-1:05 pm

1 stop26h 55m

$394

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sun 8/24

7:40 am-4:46 pm

3 stops33h 06m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Best time to book a flight from Trinidad to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Trinidad with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Trinidad to New Windsor

What is the cheapest month to book a flight from Trinidad to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Trinidad to New Windsor (average of $109). Flying from Trinidad to New Windsor in December is currently the most expensive (average of $202). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Trinidad to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Trinidad?

    For a flight from Trinidad to New Windsor, you will be flying into Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

  • Can I find deals for flights from Trinidad to Stewart that include hotel bookings?

    Yes. In addition to deals on Trinidad to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Trinidad to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Trinidad to Stewart.

  • Can I find deals for business class flights from Trinidad to Stewart?

    Yes. Cheapflights offers flight deals from Trinidad to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Trinidad to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Trinidad to New Windsor (average of $109). Flying from Trinidad to New Windsor in December is currently the most expensive (average of $202). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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